Plant growth control

ABSTRACT

The growth of unwanted weed seeds and seedling weeds is inhibited by applying to the locus thereof a herbicidal composition containing one or more substituted 3-pyridylmethanes as the herbicidally active ingredient. The growth of suckers on tobacco plants is controlled by applying these compositions to the growing plants.

United States Patent Krumkalns et al.

1151 3,655,359 1451 Apr. 11,1972

[54] PLANT GROWTH CONTROL [72] Inventors: Eriks V. Krumkalns; Hamid M. Taylor,

both of Indianapolis, Ind.

[ 73] Assignee: Eli Lilly and Company, Indianapolis, Ind. [22] Filed: Oct. 16, 1969 [21] Appl. No.: 867,058

Related U.S. Application Data [63] Continuation-in-part of Ser. No. 785,737, Dec. 20,

1968, abandoned.

[52] U.S. Cl ..7l/94,7l/78,7l/9O [51] Int. Cl. 1 ..A0ln 9/22 [58] FieldofSearch ..7l/78,94

[5 6] References Cited UNITED STATES PATENTS 3,396,224 8/1968 Van Heyningen ..424/275 I OTHER PUBLICATIONS Novikov et al. Stimulators of Plant Growth Chem. Abst. Vol. 61 (1964) 8829d Saur Milch Comparative Wheat Germination Tests with Compounds of the Pyridine Series Chem. Abst. Vol. 57 (1962) 1316F Primary Examiner-Lewis Gotts Assistant ExaminerCatherine L. Mills Attorney-Everet F. Smith and Leroy Whitaker [5 7] ABSTRACT The growth of unwanted weed seeds and seedling weeds is inhibited by applying to the locus thereof a herbicidal composition containing one or more substituted 3-pyridylmethanes as the herbicidally active ingredient. The growth of suckers on tobacco plants is controlled by applying these compositions to the growing plants.

9 Claims, N0 Drawings PLANT GROWTH CONTROL CROSS-REFERENCE This application is a continuation-in-part of our co-pending application, Ser. No. 785,737 filed Dec. 20, 1968, now abandoned.

BACKGROUND OF THE INVENTION In the prior art, DAmico, US. Pat. No. 3,155,671 Nov. 3, 1964) teaches the preparation of derivatives of 2- thiopyridine-l-oxide, which destroy or control undesired vegetation.

Johnson et al., Belgian Pat. No. 645,271 Sept. 16, 1964), teach the use of 4-hydroxytrihalo (or tetrahalo) pyridines as herbicides. These pyridine compounds were applied to the foliage of cucumber plants and wild grass to kill the wild grass.

In addition, Kovikov et al., Khim v. Selsk. Khoz. 4(6), 435-7(l966), tested semiand thiosemicarbazones of 2-, 3-, and 4-pyridinecarboxaldehyde and teach the thiosemicarhazone of 2-pyridinecarboxaldehyde as having the highest herbicidal activity.

SUMMARY This invention relates to novel processes for eliminating germinating weed grasses and broadleaf weeds and to compositions useful in these novel processes. More particularly, this invention concerns novel herbicidal processes employing compositions in which a substituted 3-pyridylmethane is the herbicidally active ingredient.

It is an object of this invention to provide compositions which are toxic to both grasses and broadleaf weeds in both their germinating and seedling stages, but which compositions are relatively nontoxic to crop plants. It is a further object of this invention to provide novel compositions and processes which can eliminate weed grasses and certain broadleaf weeds selectively from crop plants such as corn, cotton, and soybeans, and their close relatives in the plant kingdom. It is still another object of this invention to provide novel compositions and processes which inhibit the growth of suckers on tobacco plants.

DESCRIPTION OF THE PREFERRED EMBODIMENT One embodiment of the novel process of this invention comprises applying to an area infested with weed seeds and seedling weeds a herbicidal amount of one or more substituted 3-pyridylmethanes having the following formula:

wherein X is hydrogen, hydroxyl, C -C alkoxy, amino, or cyano; V V

(Q)D C1-C5 alkoxy, 01*012 alkyl, C2C3 alkenyl, C2-C3 alkynyl, C -C cycloalkyl, C -C cycloalkenyl;

R is R, pyridyl, or thienyl;

In another embodiment of the process of this invention a composition containing one or more of the above-described pyridylmethanes is applied to growing tobacco plants to inhibit the growth of laterals, or suckers, on such plants.

While a number of substituents have been indicated for the phenyl groups in the above formula, it will be apparent to those skilled in the art that other substituents may also be used, and that substitution may occur on other than the phenyl groups. When there is more than one substituent present they may be the same or different. Compounds bearing such substituents are thus to be considered to be within the scope of this invention.

In the above formula, C -C alkoxy can be, for example, methoxy, ethoxy, isopropoxy, butoxy, pentoxy, and hexoxy.

The C -C alkyl groups can be, illustratively, methyl, ethyl,

propyl, isopropyl, n-butyl, sec.-butyl, tert.-butyl, n-amyl,

isoamyl, sec.-amyl, n-hexyl, isohexyl, sec.-hexyl, n-heptyl, isoheptyl, sec.-heptyl, n-octyl, sec.-octyl, isooctyl, nonyl, decy], undecyl, dodecyl, and the like.

C -C cycloalkyl can be, illustratively, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl.

The alkenyl and alkynyl groups can be such as vinyl, allyl, lbutenyl, Z-pentenyl, 2-octenyl, l-butynyl, 2-propynyl, 2-hexynyl, and l-octynyl.

Suitable cycloalkenyl groups include cyclohexenyl, cyclopentenyl, cyclobutenyl, cyclooctenyl, and norbornenyl.

Halo includes chlorine, bromine, iodine, and fluorine.

The acid addition salts of the compounds represented by the general formula supra are represented by those formed with hydrochloric, hydrobromic, hydriodic, sulfuric, nitric, ptoluenesulfonic, maleic, acetic, and malonic acids and the like.

Examples of compounds which have the desired activity and which can be successfully employed as weed-killing agents and tobacco desuckering agents in accord with the novel processes of this invention include, but are not limited to, the following:

a-(4-chlorophenyl)-a-cyclopropyl-3-pyridinemethanol a,a-Bis(2-chlorophenyl)-3-pyridinemethanol hydrochloride a-(2,4-Dichlorophenyl)-a-(4-fluorophenyl)-3- pyridinemethanol hydrochloride a-(4-Fluorophenyl)-a-phenyl-3-pyridinemethanol hydrochloride a,a-Bis(n-pentyl)-3-pyridinemethanol hydrochloride pyridinemethanol hydrochloride a-(n-Hexyl)-a-methyl-3-pyridinemethanol 3-( 1-Isobutyl-3-methylbutyl)pyridine a,a-Bis(isobutyl)-3-pyridinemethanol a-(2,5-Dimethylphenyl)-a-phenyl-3-pyridinemethanol hydrochloride a-Chloro-a,a-bis-(4-chlorophenyl)-3-pyridylmethane hydrochloride a,a-Bis-(4-chlorophenyl)-3-pyridylmethylamine hydrochloride a,a-Bis-(4-chlorophenyl)-3-pyridylmethyl methyl ether a-Cyclobutyl-a-(4-fluorophenyl)-3-pyridinemethanol a-Pentafluorophenyl-a-phenyl-3-pyridinemethanol 3-(a-Methyl-4-chlorobenzyl)pyridine hydrochloride 3-(Dicyclohexylmethyl)pyridine a,a-Bis(cyclohexyl)-3-pyridinemethanol a,a-Bis(isopropyl)-3-pyridinemethanol a,a-Bis(isopentyl)-3-pyridinemethanol hydrochloride a,a-Bis( n-hexyl )-3-pyridinemethanol hydrochloride a,a-Dipheny]-3-pyridineacetonitrile a-(3-Ethyl-n-pentyl)-a-isobutyl-3-pyridinemethanol hydrochloride a,a-Bis(cyclopropyl)-3-pyridinemethanol hydrochloride a,a-Bis( n-propyl)-3 -pyridinemethanol hydrochloride a,a-Bis(4-iodophenyl)-3-pyridylmethane fonate a-Phenyl-a-(4-chlorobenzyl)-3-pyridylmethane a-PhenyLa-(2-thienyl)-3-pyridylmethane a-(4-chlorophenyl)-a-(2-thienyl)-3-pyridylmethane maleate a-( 3 ,4-dichlorobenzyl )-a-( 3-chlorophenyl )-3-pyridylmethane a-(4-methylthiophenyl)-a-phenyl-3-pyridylmethane 3-(a-n-Butylbenzyl)pyridine a-(4-Ethoxyphenyl)-a-phenyl-3-pyridylmethane hydrobromide a,a-Bis(4-ethylphenyl )-3-pyridylmethane oxalate a,a-Bis( 4-nitrophenyl)-3-pyridylmethane a-( 3-Bromophenyl )-a-plienyl-3-pyridylmethane sulfate a,a-Bis( 3-bromophenyl )-3-pyridylmethane nitrate a-Cyclopentyl-a-(4-chlorophenyl)-3-pyridylmetbane a-Cyclohexyl-a-( 3-bromophenyl)-3-pyridylmethane a-(2Chlorobenzyl)-a-cyclooctyl-3-pyridylmethane a-Phenyl-a-( 3-thienyl)-3-pyridylmethane a-( 4-Chlorophenyl )-a-( 2-pyridyl )-3-pyridylmethane a-Cyano-a-phenyl-a-( 3-thienyl)-3-pyridylmethane Tri-(3-pyridyl)methane a,a-Bis-( 4-iodophenyl)-3-pyridinemethanol a-( 2-Fluorophenyl)-a-phenyl-3-pyridinemethanol a-Vinyl-a-phenyl-S-pyridinemethanol a,a-Bis-( 4-chlorophenyl)-3-pyridylmethyl acetate a-Phenyl-fi-( 2-pyridyl)-a-( 3-pyridyl )ethyl acetate a-(4-Bromophenyl )-a-phenyl-3-pyridinemethanol a-(4-Chlorobenzyl)-a-allyl-3-pyridinemethanol a-( 4-Methyl-3-chlorophenyl )-a-( 2-thienyl)-3- pyridinemethanol a-( 2-Butenyl )-a-( 4-methoxybenzyl)-3-pyridinemethanol a-(4-Iodobenzyl)-a-(4-pyridyl)-3-pyridinemethanol a,a-Bis-(2-phenylethyl)-3-pyridinemethanol a-n-Amyl-a-n-hexyl-3-pyridinemethanol a,a-Bis( n-undecyl)-3-pyridinemethanol a-n-Hexyl-a-n-heptyl-3-pyridinemethanol a,a-Bis( cyclohexylmethyl)-3-pyridinemethanol hydrochloride a-Isopentyl-a-isohexyl-3-pyridinemethanol hydrochloride a-n-Undecyl-a-n-nonyl-3-pyridinemethanol sulfate a,a-Bis(isopentyl)-3-pyridinemethanol hydrobromide a-n-Dodecyl-a-n-octyl-3-pyridinemethanol phosphate a,a-Bis( n-hexyl)-3-pyridinemethanol sulfate a,a-Bis(n-undecyl)-3-pyridinemethanol phosphate a,a-Bis(sec.-nonyl)-3-pyridinemethanol oxalate a,c:-Bis(n-dodecyl )-3-pyridinemethanol hydrochloride a,a-Bis(undecyl)-3-pyridinemethanol hydrochloride a,a-Bis(n-octyl)-3-pyridinemethanol hydrobromide, and

the like.

The preferred compounds, both for herbicidal use and to inhibit tobacco sucker growth, are those in which X in the above formula is hydrogen or hydroxyl.

The compounds are formulated for use either as dusts, spray concentrates, spreadable granules, or wettable powders. Those compounds which are soluble in water are readily formulated as emulsion-type sprays or wettable powders. Compounds which are less soluble in water are desirably formulated with a wetting agent or surfactant for the preparation of emulsion-type sprays or wettable powders. The wetting agent or surfactant used in formulating the emulsion-type sprays or wettable powders can be, illustratively, polyoxyethylene sorbitan monooleate, polyoxyethylene sorbitan monolaurate, polyglycol ether sulfonate, alkylamine dodecylbenzenesulfonate, and the like. In the preparation of spreadable granules, the solid diluent used can be calcined attapulgite clay. Dry dispersions can be prepared on herbicidally inert carriers such as vermiculite, peat moss and the like.

The novel herbicidal processes of this invention comprise the treatment of a soil area or locus infested with weed grass seeds, broadleaf weed seeds and seedling weeds with a spray, a dust, or a granular formulation containing, as the herbicidally active ingredient, a compound coming within the scope of the p-toluenesulabove generic formula. Typical of soil areas upon which the instant formulations can be used as preemergent herbicides are crop-growing areas wherein corn, cotton, or soybeans are being grown. Other miscellaneous places which can be treated include gravel driveways, clay tennis courts, walks, road shoulders, and the like, where the elimination of weeds and grasses is desired. When used as complete herbicides in these latter locations, the compositions of this invention are preferred over the older forms of complete herbicides such as sodium arsenite or aminotriazole because of the lower mammalian toxicity exhibited by the instant pyridine compounds. Compositions containing the herbicidally active compound are sprayed or dusted by methods well known to the art onto the particular area at the rate of around 2 to 8 lb./acre or somewhat more if necessary; for example, 10 lb. of active ingredient per acre. For most field applications, it is preferred to spray the herbicidal compositions of this invention at the rate of about 2 to about 10 lb. of active ingredient per acre. If, however, the herbicidal compositions are spread in a granular form over the area to be treated, it is preferred to employ a greater amount of active material per acre, suitably in the range of about 4 to about 10 lb. of an active substituted 3- pyridylmethane.

Seedlings and germinating weed seeds of many varieties of grasses are killed by the above treatment process, including both undesirable grasses such as the crabgrasses (Digitaria sanguinalis and Digitan'a ischaemum); green and yellow foxtails (Setan'a vin'dis and Setan'a glauca), and the like, as well as seeds and seedlings of mustard (Brassica juncea), and pigweed (Amaranthus retroflexus). Field corn (Zea maize), cotton, and soybeans (Glycine max) are unafi'ected by preemergent application of the herbicidal compounds, although the compounds have postemergent herbicidal action against these last named crops, and against the crabgrasses, mustard, pigweed, foxtail and velvetleaf as well.

Preemergent application of sprays or dusts containing a compound of this invention as represented by the above formula, at the rate of about 8 lb. herbicidal compound per acre to an area infested with foxtail and crabgrass seeds, provided complete control of these undesirable grasses.

When sprays or dusts containing a compound represented by the generic formula, supra, are applied at the rate of about 8 lb. of herbicidal compound per acre to test flats planted with crops, for example, corn, cotton, soybeans, and infested with foxtail, crabgrass, mustard, pigweed, and velvet leaf, control of the weed species is obtained without harm to the crop plants.

The herbicidal compositions of this invention can be employed in other useful ways. For example, spray or dust compositions as provided by this invention can be used to eradicate crabgrass, mustard, and foxtail from perennial flower beds or to destroy germinating seeds of an undesired grass in turf. Other methods of employing the selective herbicidal compositions of this invention will be readily apparent to those skilled in the art.

The compounds useful in this invention are conveniently prepared by methods well known to the art. Thus, the 3- pyridyl-methane derivatives are readily synthesized by the methods taught by Van Heyningen et al., US. Pat. No. 3,397,273 Aug. 13, 1968); and the B-pyridinemethanols and derivatives thereof are made available by methods taught by Van Heyningen, US. Pat. No. 3,396,224 Aug. 6, 1968). In particular, the a,a-dialkyl-substituted 3-pyridinemethanols are prepared according to the teaching of Wibaut et al., Rec. Trav. Chim, 77, 1,057, 1958).

A number of the herbicidal methods and compositions of the present invention are illustrated by the following specific examples.

EXAMPLE 1 The following experimental procedure was used to demonstrate the efficacy of the compositions of this invention in killing germinating grasses without afiecting the germination of seeds and the growth of seedlings of various broadleaf and leguminous plants.

A soil was prepared consisting of one part masonry sand and one part shredded top soil blended together in a cement mixer. One gallon of this soil was placed in a 25 X 35 cm. galvanized flat and was patted down with a bench brush until level. A three-row marker was used to make 2 93cm. furrows in approximately two-fifths of the flat. Crop seeds consisting of four kernels of corn, five cotton seeds, and five soybean seeds were placed in these furrows. A four-row template was then placed on the remaining soil and the indicated amounts of each of the following seeds were planted, one species to each section: foxtail, 100 mg.; velvet leaf (Abutilon theophiasti), 50-75 mg.; rough pigweed (Amaranthus retroflexus), 30-50 mg.; and large crabgrass, 350-400 mg. Sufficient soil was added to cover the entire flat. Thus, the weed seeds were covered to a depth of about 6 mm. and the crop plant seeds were covered to a depth of about 3 cm.

In assaying the effect of the compositions as preemergent herbicides, a flat prepared as above was placed in a chamber equipped with a turntable and an air exhaust. The herbicidal composition, whether it was a spray-type emulsion formulated from the growth-inhibiting compound in combination with a wetting agent and a nonphytotoxic, inert diluent such as acetone, cellosolve, dimethylforrnamide, water, and the like,

or a wettable powder, was applied to the flat with a modified DeVilbiss atomizer hooked to an air source. 12 k milliliters of the composition under test were applied to each flat either on the day of planting or the succeeding day. For measuring the efficacy of the herbicidal compositions as post-emergent herbicides, the same experimental setup was used except that the flats were sprayed after 9 to 12 days in a greenhouse, the length of growing time depending upon the season and light intensity. lnjury ratings and observations as to type of injury were made in either case 1 1 to 12 days after treatment. The injury rating scale used was as follows:

0 no injury 1 slight injury 2 moderate injury 3 severe injury 4 death When more than one determination was carried out, an average value was calculated for the injury rating.

Tables 1 and 11 which follow set forth the results of preemergent and post-emergent testing of several substituted 3- pyridylmethanes, substituted 3-pyridinemethanols, and salts thereof. In both tables, Column 1 gives the name of the compound; Column 2, the rate in terms of pounds per acre at which the compound was applied to the test flat; and Columns 3 to 9, the injury rating for the particular plant seedlings or m ature plants.

TABLE I.IN.TURY RATING ON PRE-EMERGENT TREATMENT Lb./ Cot- Soy- Crab- Pig- Fox- Velvet- Compound acre Corn ton beans grass weed tail leaf 3-[Bis(4-fluorophenyl)methyl] pyridine 8 0 0 0 3 3 2 0 4 0 0 O 2 4 3 0 2 0 0 0 2 1 2 0 a- 4-Fluorophenyl)u-pheny1-3-pyridinemethanol hydrochloride 8 0 0 0 2 3 2 0 w(2-Chlorophenyl)-a-(4-fluomphenyl)-3- pyrldinemcthanol hydrochloride 8 0 0 0 3 3 3 1 4 0 0 0 3 0 2 0 m-(2,5-Dlmethylphenyl)-aphenyl-3-pyridinemethanol hydrochloride 8 0 0 0 3 4 3 2 4 0 0 0 3 2 1 1 2 0 0 0 3 2 0 0 a-(2,5 Dichlorophenyl)-a-(4-fluorophenyl)-3- pyrldinemethanol hydrochloride 8 0 0 0 2 4 3 0 a-Cyclobutyl-a-(4-fluorophenyl)-3-pyridinemethanol 8 0 0 0 3 3 2 2 4 0 0 1 3 3 3 1 2 0 0 0 3 3 3 1 a,a-Bis(cyclopropyl)-3-pyridinc-methanol hydrochloride 8 0 0 0 3 3 3 2 4 0 0 0 2 0 1 1 a ,a-Bis(cyclohcxyl)-3-pyridinemethanol 8 0 0 0 3 4 2 1 3[a-Cyclohexyl-a-(leyclohexenyl)-methyl] pyridine 8 1 O 0 4 4 3 3 4 0 0 0 3 4 2 1 2 0 0 0 3 2 3 0 1 0 0 0 3 4 2 0 a,cr-Bl5(1lentyl)-3-pyridincmethanol hydroch oride 8 0 0 0 3 3 2 0 mar-Bis(isobutyl)-3-pyridinemethanol 8 1 0 0 3 4 3 4 4 0 0 0 3 4 3 3 2 0 0 0 3 4 2 2 a,a-Bis(isopentyl)-3-py!idinemethanol hydrochloride 8 0 0 0 3 4 3 2 4 0 0 0 2 2 2 0 1!,a-B is (n-propyl) -3-pyridinemethanol hydrochloride 8 1 0 1 3 4 3 1 4 0 0 0 3 3 3 0 a-(n-Pentyl)a-phenyl-3-pyridinc-methanol hydrochloride 8 0 0 0 4 4 3 2 4 0 0 0 2 1 1 0 a,a-Dipheny1-3-pyridineaeetonitrile 8 0 0 0 3 2 3 0 4 0 0 0 3 2 3 1 2 0 0 0 3 1 1 0 1 0 0 0 3 1 0 0 3-(a-MethyM-chlorobenzyl) pyridine hydrochloride 8 1 0 0 3 4 3 3 4 0 0 0 2 U 3 0 cx-(3-E thyl-n-pentyl)-Q-iS0butyl-3-pyridine methanol hydrochloride 8 0 0 0 4 2 3 2 a-(nHeptyl)-a-isobuty1-3-pyridlne methanol 8 0 1 2 3 3 3 3 V 7 4 o 0 0 3 4 3 3 TABLE I.-INJUR Y Range} QQT EB IQEMEQQHT TBEAEMEN'I-(ominuul LbJ Cot- Soy- Crab- P1 Fox- Velvet Com oonnd acre Corn ton beans grass weed tall lent a,a-Bismyclohexy1rnethyD-3-pyridine methanol c, 8 0 0 3 3 2 1 ,a-DiphrznybS-pyridinemethanol hydrochloride 8 0 1 0 3 3 1 1 a-(2-CMorn-5mitrophnnyI)a-phenyl-3- )yridlnemethanol 8 0 0 O 2 4 2 0 3- lilslhhlorcguhcnyl)methyll-pyrl he hydrochlorl e r 1 8 O 0 0 3 O 3 l 2-(3-lyri'lyl)-2-hexanol 8 0 1 1 4 3 3 fil-lyridyl)-5-hy iroxynonane 8 0 0 1 4 2 3 a,a-Blslcyclohexylmethyl)-3-pyridinemethanol hydrochloride 8 0 0 0 3 3 2 1 a,a-Bls(n'butyl)-3-pyrldinemethanol hydrochloride. 8 0 0 0 3 4 3 3 a-(4-Chloroohenyl)-a-cyclopropyl-3-pyridinemethanol 8 0 0 0 4 4 3 2 4 0 0 0 3 3 3 2 2 0 0 0 2 2 2 l w t- I -lnmohenyl)-a-cyclopropyl-3-pyridlnemethanol hydrochloride 8 0 0 2 4 4 3 2 4 0 0 1 3 4 3 1 2 O 0 O 3 1 3 l a-(4-Chlorophenyl)-wethynyl-3-pyrldinemethanol 8 0 0 2 3 4 3 2 4 0 0 1 3 4 3 1 2 0 0 0 1 0 2 1 a-Phenyl-wQ-thienyl)-3-pyridinemethanol hydrochloride 8 0 O 2 3 4 3 0 4 0 0 0 2 2 2 0 a-Isopropyl-a-phenyl-3-pyridine-methanol 8 0 0 2 3 4 3 2 4 0 0 0 3 4 2 2 2 O 0 0 2 2 2 2 ot-Bis(cyelopropyl)-3-pyridinernethanol hydrochloride l 8 0 0 O 3 4 3 2 4 0 0 0 2 0 1 1 a,a-Bis(cyclopropyl)-3-pyridinemethanol 8 0 0 3 4 2 3 v 3 4 0 O 0 3 4 2 1 TABLE II.INJURY RATING 0N PRE-EMERGENT TREATMENT Lb./ Soy- Crab- Iig- Fox- Velvet- Compound acre Corn Cotton beans grass weed tail leaf B-[Bis l-fluorophenyl) methyll pyri dine s 8 0 1 4 3 4 3 0 4 1 2 2 1 2 1 1 2 1 2 2 1 1 1 1 0,!2'B is (isobutyl) -3-pyridine-methanol 8 1 2 2 3 4 2 1 4 O 1 2 1 2 1 1 a,a-Bis(cyclopropyl)-3-pyridine-methanol hydrochloride 8 1 1 2 3 4 2 2 4 0 0 1 2 1 0 1 3-(a-Methyl-ichlorobenzyl)-pyridine hydrochloride 4 8 2 3 2 3 4 3 4 4 0 1 2 2 2 2 2 3-[1-(n-Hepty1)-n-octyl]-pyridine 8 0 1 2 3 4 3 2 4 1 1 2 1 4 2 2 a-(n-Heptyl) -a-isobutyl-3-pyridinemethanol 8 1 1 2 3 3 1 2 a,a-Diphenyl-3-p ridineacetonitrile 8 1 1 3 2 2 1 1 a,a-Bis(isopentyl -3-pyridinemethanol hydrochlon' do 8 0 1 2 2 2 2 2 a,a-Diphenyl-3pyridinemethanol hydrochloride 8 1 1 3 1 1 1 1 at-Bis(n-butyi)-3-pyridine-methanol hydrochloride 8 0 0 l 2 4 2 4 4 0 0 1 2 3 1 4 To control the growth of stickers on tobacco plants the were measured, and the growth of suckers on treated plants compounds described herein are applied to growing tobacco was compared to growth on untreated controls. One, two, or plants at a rate of 0. l to 2 lbs. per acre. For such application three comparisons were made at intervals of l to 2 weeks. In the compounds are formulated into sprays or wettable powsome cases, after the third measurement the suckers were ders as described above and applied to the foliage of the removed weighed F the E 0t Suckers treated plants. We have seen no injury to the tobacco plants at the Plants compared 2 f 9 Suckers from control rates used. The inhibition of sucker growth will be illustrated P Percent of mhlbmon was calculated from the by the following example. followlng formula- EXAMPLE 2 Percent inhibition Control measurement-treated measurement Growing tobacco plants were topped, suckers over 1 inch in X 100 Control measurement length were removed, and each plant was sprayed with 20 m]. of a formulation containing the concentration of the test compound indicated in parts per million. The suckers on the plants The results are summarized in Table III.

Table III.Tobacco Sucker Control Percent inhibition 3[1-(2-chlorophenyl)-n-heptyl]pyridine 500 30. 1 51. 1, 000 35. 45. 6 2, 000 78. 6 77. 0

3[a-(n-pentoxy)benzyl1-pyridine 500 27. 2 24. 7 1, 000 24. 5 13. 2 2, 000 43. 9 41. 4

2-(Z-ChIOIO-zx-CYClOhGXYl-bBIlZYi) pyridine- 500 10. 6 7. 8 1,000 14. 1 8. 7 2, 000 10. 1 8. 3

4-(4-pyridyl) heptanol-4 500 9. 5 0 0 1, 000 18. 1 2. 7 36. 6 2, 000 18. 1 4. 0 87. 2

ar-bis(n-pentyl)-4-pyrldinemethanol. 500 0 O 0 1,000 30.3 1.0 57.6 2,000 7.7 1.3 35.7 a-(4chl0r0phmly1)-a-(2,4 di0h10f0benZyl) 3- pyridinemethanol sulfate 500 0 0 O 1,000 42. 5 53.8 58.8 2, 000 0 9. 7 0 1 3-(l,Q-diphenylothyl)pyridine 500 40. 4 25. 2 1, 000 58. 2 63. 7 2, 000 47. 5 65. 8

methanol hydrochloride 2, 000 55. 4 77. 0 87. 1 4

2-(3-pyridyl)-1-(-l-chloropheny1)2-2-propanol. 500 55 1,000 2, 000 u-(npentyl)wx-phenyl-apyridinemethanolhydroehlorlde 2, 000 43.1 35 5 28.5 47.6

t x-bis(cyclohexyl)-3-pyridlnemethanol 2,000 01.1 00 2 81.1 )1 0 4,000 70.3 07 2 70.3 3-pyridyl4-chlorophenyl-4-chlorobenzylcarbinol 500 60.6 1,000 27.6 2,000 0 a-(4-chloropheny1)-a-eyclopropyl-3 pyridinemethanol hydrochloride 2,000 01.1 2 85.6 91 4 3-pyridyldiphenyl-methane- 500 30.8 20.6 0 1,000 45.3 44.6 2 8 2, 000 75.1 78.6 56 9 3-[a-(2,5-dimethylphenyl)benzyl]-pyridine 2, 000 93.9 98.4 99 1 99.7 4,000 88. 2 95.1 97 3 99 5 a-(2-ehlorophenyl)u-cyclohexyl-2pyridinemethanol 500 51.3 48.6 56 2 1,000 74.7 56.1 61 4 2,000 0 3-[bis(4-chlorophenyl)methyllpyridlne hydrochloride 500 1, 000 2, 000

B is (4-chlorophenyl) -3-pyridy1n1ethane 3-bis(2,5-diehlorophonyl)methylpyridine 880 1, 0 2, 000

3 dicyelohexylmethyl-pyridine 88g 1t will be noted that 3-ay dhzhlorodiphenylmethyl)- '7 m herein have been found to exhibit general plant growth inpyridine is an especially active compound. Its activity is 70 hibiting activity, especially with regard to foliar growth. For somewhat different from presently used tobacco desuckering example, the application of 3-(2,2-dichlorodiphenyl)pyridine agents in that it appears not only to depress the formation of to blue grass at a rate of 0.4 to 10 lbs/acre retards the growth new suckers, but also removes small suckers as well. of the grass leaves, thereby requiring less frequent mowing.

In addition to the above-described herbicidal and tobacco The application of a-(4-chlorophenyl)-a-cyclopropyl-3- des uckering activity, the pyridine compounds described 75 pyridinemethanol to mature soybeans at a rate of 0.4 to 10 2 seeds and seedling weeds which comprises applying to said lbs/acre retards foliar growth, permitting the plant to devote all its energy to fruit growth.

In general, application of the compounds may be as a foliar spray or a soil drench using techniques well known to those skilled in the art. At times, treatment may be effected by a 5 seed soak treatment. in this method of treatment the seeds to be treated are allowed to stand in a solution of the compound for a period of several hours. The solution is prepared by dissolving the compound in an inert solvent such as acetone and diluting to the desired concentration with water containing a surface active agent.

We claim:

l. A method for inhibiting the growth of germinating weed seeds and seedlings a herbicidally effective amount of a com- P u d fit lsf mvla M X 3H. I N wherein X is hydrogen, hydroxyl, C C; alkoxy, amino,

alkcnyl, C -C cycloalkenyl; R

each Q independently is halo, nitro, C -C alkyl, C -C alkoxy, trifluoromethyl, C -C alkylthio, C -C alkyl-SO, or C,C alkylSO or two Qs taken together are methylenedioxy; each 11 independently is an integer of 0 to 3; and m is an integer of l to 3; and the acid addition salts thereof.

2. A method as in claim 1 wherein the compound is applied at a rate between about 2 and about 8 lbs. per acre.

3. A method as in claim 1 wherein X is hydrogen.

4. A method'as in claim 3 wherein the compound is 3-[acyclohexyl-a-( 1-cyclohexenyl)methyl]pyridine.

5. A method as in claim 3 wherein the compound is 3-[bis(4 -fluorophenyl )methyl lpyridine.

6. A method as in claim 1 wherein X is hydroxyl.

7. A method as in claim 6 wherein the compound is (1,0:- diisobutyl-El-pyridinemethanol.

8. A method as in claim 6 wherein the compound is a-( 2,5- dimethylphenyl)-a-phenyl-3-pyridinemethanol hydrochloride.

9. A method as in claim 6 wherein the compound is acyclobutyl-a-( 4-fluorop hen yl S- yrid inemethanOl. 

2. A method as in claim 1 wherein the compound is applied at a rate between about 2 and about 8 lbs. per acre.
 3. A method as in claim 1 wherein X is hydrogen.
 4. A method as in claim 3 wherein the compound is 3-( Alpha -cyclohexyl- Alpha -(1-cyclohexenyl)methyl)pyridine.
 5. A method as in claim 3 wherein the compound is 3-(bis(4-fluorophenyl)methyl)pyridine.
 6. A method as in claim 1 wherein X is hydroxyl.
 7. A method as in claim 6 wherein the compound is Alpha , Alpha -diisobutyl-3-pyridinemethanol.
 8. A method as in claim 6 wherein the compound is Alpha -(2,5-dimethylphenyl)- Alpha -phenyl-3-pyridinemethanol hydrochloride.
 9. A method as in claim 6 wherein the compound is Alpha -cyclobutyl- Alpha -(4-fluorophenyl)-3-pyridinemethanol. 